Dichloromethane → HCID 86650643、化合物

HRID 1623399ノート

反応式

HRID 1623399 の反応式
Br[C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)[CH:5]=[CH:4][CH:3]=1.[Cl:17][C:18]1[CH:23]=[C:22](B(O)O)[C:21]([O:27][CH3:28])=[CH:20][N:19]=1.C(Cl)Cl>COCCOC.C([O-])([O-])=O.[Na+].[Na+].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:17][C:18]1[CH:23]=[C:22]([C:2]2[CH:3]=[CH:4][CH:5]=[C:6]([NH:8][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=3)[N:7]=2)[C:21]([O:27][CH3:28])=[CH:20][N:19]=1

参加物

7

反応物 3

HCID 6344DichloromethaneHCID 46738707B-(2-Chloro-5-methoxy-4-pyridinyl)boronic acidHCID 581273766-bromo-N-(3-fluorobenzyl)pyridin-2-amine

生成物 1

HCID 86650643HCID 86650643、化合物収率 7.8%

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 80711,2-Dimethoxyethane溶媒HCID 10340Sodium Carbonate溶媒

反応条件

温度
110 °C

実験手順

To a solution of 6-bromo-N-(3-fluorobenzyl)pyridin-2-amine (555 mg, 1.974 mmol) and 2-chloro-5-methoxypyridin-4-ylboronic acid (518 mg, 2.76 mmol) in DME (4 ml) and 2M Na2CO3 aq (2 ml) was added PdCl2(dppf).CH2Cl2 adduct (81 mg, 0.099 mmol). This was then heated at 110° C. for 5 h. The reaction mixture was allowed to cool and then the DME was evaporated under reduced pressure. The resulting residue was partitioned between EtOAc and water. The organics were combined, then washed with H2O (×3), saturated aq. brine (×3), then dried (Na2SO4), filtered and evaporated under reduced pressure. The resulting residue was purified by flash column chromatography (silica gel; 15% to 25% EtOAc/hexane) to give 2′-chloro-N-(3-fluorobenzyl)-5′-methoxy-2,4′-bipyridin-6-amine (53 mg).

後処理

  1. temperatureto cool
  2. customthe DME was evaporated under reduced pressure
  3. customThe resulting residue was partitioned between EtOAc and water
  4. washwashed with H2O (×3), saturated aq. brine (×3)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe resulting residue was purified by flash column chromatography (silica gel; 15% to 25% EtOAc/hexane)

出典と根拠

ORDレコード
ord-48c994532d3d48eda44610a2ab68197a
出典データセット
uspto-grants-2014_07
特許番号
US08778951B2

反応ノート

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